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Volumn 56, Issue 19, 2000, Pages 2967-2974

Synthesis of 2-(α-substituted N-tosylaminomethyl)-2,5-dihydrofurans by reaction of N-sulfonylimines with arsonium or sulfonium 4-hydroxyl-cis-2- butenylides

Author keywords

Aziridination; Dihydrofuran; N tosylimines; Ylide

Indexed keywords

FURAN DERIVATIVE; IMINE;

EID: 0034608034     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00191-5     Document Type: Article
Times cited : (19)

References (49)
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    • A review on the structure of 2,5-dihydrofurans: (a) Katritzky, A. R., Charles, W. R., Eds., Pergamon Press: Oxford
    • A review on the structure of 2,5-dihydrofurans: (a) Dean, F. M., Sargent, M. V. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Charles, W. R., Eds., Pergamon Press: Oxford, 1984; Vol. 4, pp 531-597. A leading paper on the NMR study of 2,5-dihydrofurans:
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    • Other than typical methods for preparing 2,5-dihydrofurans, the reaction of α,β-unsaturated ketones with dimethylsulfonium methylide, or the intramolecular cyclization of allenic alcohols
    • Other than typical methods for preparing 2,5-dihydrofurans, the reaction of α,β-unsaturated ketones with dimethylsulfonium methylide (Bravo, P.; Ticozzi, C. J. Chem. Soc., Chem. Commun. 1979, 438) or the intramolecular cyclization of allenic alcohols (Olsson, L.-I.; Claesson, A. Synthesis 1979, 743) are also available.
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    • Other than typical methods for preparing 2,5-dihydrofurans, the reaction of α,β-unsaturated ketones with dimethylsulfonium methylide (Bravo, P.; Ticozzi, C. J. Chem. Soc., Chem. Commun. 1979, 438) or the intramolecular cyclization of allenic alcohols (Olsson, L.-I.; Claesson, A. Synthesis 1979, 743) are also available.
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    • A discussion on the reactivities of 2,5-dihydrofurans: Katritzky, A. R., Charles, W. R., Eds., Pergamon Press: Oxford
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    • Recent publications on the synthetic applications of 2,5-dihydrofurans: (a)
    • Recent publications on the synthetic applications of 2,5-dihydrofurans: (a) Kang, S. H.; Lee, S. B. J. Chem. Soc., Chem. Commun. 1995, 1017.
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    • Ph.D. Thesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 1996
    • Li, A.-H. Ph.D. Thesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 1996.
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    • Due to the susceptibility of compound 14a to ring closure, pure 14a is very difficult to obtain. It is stable in dichloromethane, at room temperature, but the aziridine ring can be opened to produce compound 4a, when the solvent is evaporated, even at -78°C
    • Due to the susceptibility of compound 14a to ring closure, pure 14a is very difficult to obtain. It is stable in dichloromethane, at room temperature, but the aziridine ring can be opened to produce compound 4a, when the solvent is evaporated, even at -78°C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.